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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:32 UTC
HMDB IDHMDB0000841
Secondary Accession Numbers
  • HMDB00841
Metabolite Identification
Common NameN-Acetylgalactosamine 6-sulfate
DescriptionN-Acetylgalactosamine 6-sulfate is found in keratan sulfate and chondroitin 6-sulfate. PMID: 12489154 . Morquio syndrome is caused by an abnormal accumulation of mucopolysaccharides - in this case, keratan sulfate - in the body. Keratan sulfate is excreted in urine. The symptoms vary from patient to patient, and may include hearing loss, cataracts, skeletal dysplasia, spinal instability, and minor respiratory issues, among others. Two forms are recognized, type A and type B. Type A is a deficiency of the enzyme N-acetylgalactosamine-6-sulfate sulfatase. (Wikipedia).
Structure
Data?1563860672
Synonyms
ValueSource
N-Acetylgalactosamine 6-sulfuric acidGenerator
N-Acetylgalactosamine 6-sulphateGenerator
N-Acetylgalactosamine 6-sulphuric acidGenerator
N-Acetyl-chondrosamine 6-(hydrogen sulfate)HMDB
N-Acetyl-chondrosamine 6-(hydrogen sulphate)HMDB
Nag-6-SHMDB
N-[(2R,3R,4R,5R)-3,4,5-Trihydroxy-1-oxo-6-(sulfooxy)hexan-2-yl]ethanimidateGenerator
N-[(2R,3R,4R,5R)-3,4,5-Trihydroxy-1-oxo-6-(sulphooxy)hexan-2-yl]ethanimidateGenerator
N-[(2R,3R,4R,5R)-3,4,5-Trihydroxy-1-oxo-6-(sulphooxy)hexan-2-yl]ethanimidic acidGenerator
N-Acetylgalactosamine 6-sulfateMeSH
Chemical FormulaC8H15NO9S
Average Molecular Weight301.271
Monoisotopic Molecular Weight301.046751773
IUPAC Name{[(2R,3R,4R,5R)-5-acetamido-2,3,4-trihydroxy-6-oxohexyl]oxy}sulfonic acid
Traditional Name[(2R,3R,4R,5R)-5-acetamido-2,3,4-trihydroxy-6-oxohexyl]oxysulfonic acid
CAS Registry Number10357-00-3
SMILES
CC(=O)N[C@@H](C=O)[C@@H](O)[C@@H](O)[C@H](O)COS(O)(=O)=O
InChI Identifier
InChI=1S/C8H15NO9S/c1-4(11)9-5(2-10)7(13)8(14)6(12)3-18-19(15,16)17/h2,5-8,12-14H,3H2,1H3,(H,9,11)(H,15,16,17)/t5-,6+,7+,8-/m0/s1
InChI KeyNHZWETQZLORZIR-OSMVPFSASA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monosaccharide sulfates. These are monosaccharides that contain a sulfate group linked to the sugar moiety.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharide sulfates
Alternative Parents
Substituents
  • Monosaccharide sulfate
  • Amino saccharide
  • Beta-hydroxy aldehyde
  • Sulfuric acid monoester
  • Sulfate-ester
  • Sulfuric acid ester
  • Alkyl sulfate
  • Organic sulfuric acid or derivatives
  • Acetamide
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Polyol
  • Carboxylic acid derivative
  • Aldehyde
  • Organonitrogen compound
  • Organopnictogen compound
  • Alcohol
  • Carbonyl group
  • Organic nitrogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility18.9 g/LALOGPS
logP-1.9ALOGPS
logP-5.7ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)-2ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.46 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity58.44 m³·mol⁻¹ChemAxon
Polarizability26.16 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001l-4930000000-3995205cfc86e324a9e0JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03xr-6679430000-092e8c1002aa5cf900f1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uec-2496000000-96d63298ebd1e32237c1JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zfr-8910000000-5568627b80a529b392e2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r7-9500000000-48ef9d68c6da00796d65JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-1159-0921000000-71152529ad1ded1d5361JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pba-4910000000-cf50abbc7698ce6c52caJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5c-9400000000-9dcf49e83939f8b39debJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022274
KNApSAcK IDNot Available
Chemspider ID167877
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5804
PubChem Compound193456
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Eliakim R, Gilead L, Ligumsky M, Okon E, Rachmilewitz D, Razin E: Histamine and chondroitin sulfate E proteoglycan released by cultured human colonic mucosa: indication for possible presence of E mast cells. Proc Natl Acad Sci U S A. 1986 Jan;83(2):461-4. [PubMed:2417244 ]
  2. Chambers WH, Oeltmann TN: The effects of hexose 6-O-sulfate esters on human natural killer cell lytic function. J Immunol. 1986 Sep 1;137(5):1469-74. [PubMed:3462244 ]
  3. Sobue M, Takeuchi J, Fukatsu T, Nagasaka T, Nakashima N, Ogura T, Katoh T, Yoshida K: Immunohistochemical techniques for detection of dermatan sulfate proteoglycan in tissue sections. Stain Technol. 1989 Jan;64(1):43-7. [PubMed:2741184 ]
  4. Yutaka T, Okada S, Kato T, Inui K, Yabuuhi H: Galactose 6-sulfate sulfatase activity in Morquio syndrome. Clin Chim Acta. 1982 Jul 1;122(2):169-80. [PubMed:6809361 ]
  5. Yutaka T, Okada S, Kato T, Inui K, Yabuuchi H: Properties of sulfatases in cultured skin fibroblasts of multiple sulfatase deficient patients. Clin Genet. 1981 Oct;20(4):296-303. [PubMed:7333023 ]
  6. Yamakoshi Y, Hu JC, Liu S, Sun X, Zhang C, Oida S, Fukae M, Simmer JP: Porcine N-acetylgalactosamine 6-sulfatase (GALNS) cDNA sequence and expression in developing teeth. Connect Tissue Res. 2002;43(2-3):167-75. [PubMed:12489154 ]